It would appear the "silent install" instructions have not been truly updated in years. The writeup for 1.4.2 is the last robust writeup I can find.

What flag is needed to do a true unattended installation of the JRE or JDK? As it stands the installer will either (a) bring up the secure connection prompt in spite of being a silent install, or worse (b) hang completely.

Work blocks most image hosting sites so here is a link to the exact dialog which should NOT pop up when doing a silent install, but does anyway: http://blog.gordonturner.ca/wp-content/uploads/2009/03/tweetdeck-error.jpg

Why use the STATIC flag? Doing so overwrites the patch-in-place function. When a new version (i.e. 6u29) is installed, it will be installed as a new entity instead of updating the existing version (i.e. 6u24).

Can you just run <installer> /s ?

Also, the online installer requires network connection during install. If there's a problem, maybe you should try the offline installer?

Why use the STATIC flag? Doing so overwrites the patch-in-place function
This is by design. The machines being built are on a closed network that will throw security alerts whenever unexpected network calls are made (e.g. an auto update poll).

Can you just run <installer> /s ?
As part of the troubleshooting process I have run it with all flags in all combinations, including the basic "/s". The dialog is thrown regardless.

If there's a problem, maybe you should try the offline installer?
This is the offline installer. It's not exactly offline. Quite exasperating to be honest.